Methanol → 7-Chloro-1-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-1,8-naphthyridin-2(1H)-one

HRID 696250Notes

Reaction equation

HRID 696250 reaction equation
[C:50]([BH3-:51])#[N:52].[CH3:57][OH:58].[CH:29]([N:30]([CH:31]([CH3:32])[CH3:33])[CH2:34][CH3:35])([CH3:36])[CH3:37].[Cl:54][CH2:55][Cl:56].[F:1][C:2]([F:3])([F:4])[C:5]([OH:6])=[O:7].[NH2:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][n:17]2[c:18](=[O:28])[cH:19][cH:20][c:21]3[cH:22][cH:23][c:24]([Cl:27])[n:25][c:26]23)[CH2:13][CH2:14]1.[Na+:53].[O:38]1[CH2:39][CH2:40][O:41][c:42]2[cH:43][n:44][c:45]([CH:48]=[O:49])[cH:46][c:47]21>>[NH:8]([CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][n:17]2[c:18](=[O:28])[cH:19][cH:20][c:21]3[cH:22][cH:23][c:24]([Cl:27])[n:25][c:26]23)[CH2:13][CH2:14]1)[CH2:48][c:45]1[n:44][cH:43][c:42]2[c:47]([cH:46]1)[O:38][CH2:39][CH2:40][O:41]2

Participants

9

Reactant 8

HCID 887MethanolHCID 923Sodium ionHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 498716Cyano-borohydrideHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 866426411-[2-(4-Aminopiperidin-1-yl)ethyl]-7-chloro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 159824067-Chloro-1-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-1,8-naphthyridin-2(1H)-one

Sources & evidence

ORD record
ord-af1744cb6fd84dfba6c9dd78c45a8e28
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (3/10)

Reaction notes

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